Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H27N7O |
| Molecular Weight | 393.4854 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C1CCC(CC1)NC2=NC(NC3=CC=C(C=C3)N4CCOCC4)=NC5=C2N=CN5
InChI
InChIKey=ZFLJHSQHILSNCM-UHFFFAOYSA-N
InChI=1S/C21H27N7O/c1-2-4-15(5-3-1)24-20-18-19(23-14-22-18)26-21(27-20)25-16-6-8-17(9-7-16)28-10-12-29-13-11-28/h6-9,14-15H,1-5,10-13H2,(H3,22,23,24,25,26,27)
| Molecular Formula | C21H27N7O |
| Molecular Weight | 393.4854 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18483302
https://www.ncbi.nlm.nih.gov/pubmed/22477067
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18483302
https://www.ncbi.nlm.nih.gov/pubmed/22477067
First synthesized in 2004 by the group of Peter G. Schultz, reversine is a 2,6- diamino substituted purine showing a potent inhibition on Aurora B, a protein kinase overexpressed in a variety of solid tumors. Due to its relevance in the cell cycle regulation, Aurora B represents a good target for anti-cancer drug development, so that reversine can be used as a promising lead compound for new potential antitumor agents. Reversine is a potent human A3 adenosine receptor antagonist with Ki of 0.66 μM, and a pan-aurora A/B/C kinase inhibitor with IC50 of 12 nM/13 nM/20 nM, respectively. Reversine also inhibits Mps1. Reversine is effective in inhibiting the growth of thyroid cancer cells by cell cycle arrest or apoptosis, especially with the more aggressive ATC and PDTC. Apoptosis was induced by the mitochondria-independent pathway. Reversine is being under investigation in clinical therapeutics.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL256 |
0.66 µM [Ki] | ||
Target ID: CHEMBL4722 |
12.0 nM [IC50] | ||
Target ID: CHEMBL2185 |
13.0 nM [IC50] | ||
Target ID: CHEMBL3935 |
20.0 nM [IC50] | ||
Target ID: CHEMBL3983 |
6.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Ontology-based meta-analysis of global collections of high-throughput public data. | 2010-09-29 |
|
| Cell reprogramming: expectations and challenges for chemistry in stem cell biology and regenerative medicine. | 2010-08 |
|
| Dissecting the role of MPS1 in chromosome biorientation and the spindle checkpoint through the small molecule inhibitor reversine. | 2010-07-12 |
|
| Tumor cell-specific bioluminescence platform to identify stroma-induced changes to anticancer drug activity. | 2010-04 |
|
| Beneficial effects of reversine on in vitro development of miniature pig somatic cell nuclear transfer embryos. | 2010-04 |
|
| Reversine enhances generation of progenitor-like cells by dedifferentiation of annulus fibrosus cells. | 2010-04 |
|
| Proteomic analysis of blastema formation in regenerating axolotl limbs. | 2009-11-30 |
|
| Proteomic signature of reversine-treated murine fibroblasts by 2-D difference gel electrophoresis and MS: possible associations with cell signalling networks. | 2009-06 |
|
| The Aurora B kinase activity is required for the maintenance of the differentiated state of murine myoblasts. | 2009-02 |
|
| Reversine increases the plasticity of lineage-committed cells toward neuroectodermal lineage. | 2009-01-30 |
|
| Reversine, a novel Aurora kinases inhibitor, inhibits colony formation of human acute myeloid leukemia cells. | 2008-05 |
|
| The 2,6-disubstituted purine reversine induces growth arrest and polyploidy in human cancer cells. | 2007-12 |
|
| Induction of growth arrest and polycomb gene expression by reversine allows C2C12 cells to be reprogrammed to various differentiated cell types. | 2007-12 |
|
| Reversine stimulates adipocyte differentiation and downregulates Akt and p70(s6k) signaling pathways in 3T3-L1 cells. | 2007-06-29 |
|
| Reversine inhibits spontaneous synaptic transmission in cultured rat hippocampal neurons. | 2007-06 |
|
| Detection and functional characterization of Pgp1 (ABCB1) and MRP3 (ABCC3) efflux transporters in the PLHC-1 fish hepatoma cell line. | 2007-03-30 |
|
| Reversine-treated fibroblasts acquire myogenic competence in vitro and in regenerating skeletal muscle. | 2006-12 |
|
| Small molecules driving myotube fission. | 2005-10 |
|
| "Reversine" and its 2-substituted adenine derivatives as potent and selective A3 adenosine receptor antagonists. | 2005-07-28 |
|
| Small molecules, big plans--can low-molecular-weight compounds control human regeneration? | 2004-08-06 |
|
| Unraveling the molecular basis for regenerative cellular plasticity. | 2004-08 |
|
| Dedifferentiation? What's next? | 2004-04 |
|
| Stem cells from differentiated cells. | 2004-04 |
|
| Dedifferentiation of lineage-committed cells by a small molecule. | 2004-01-21 |
Patents
Sample Use Guides
Mice: mice were orally fed with reversine 0.1 mg/kg or reversine 1.0 mg/kg
Route of Administration:
Oral
In SW579 cells, G2/M phase arrest was found in
low-dosage treatment (1 uM) with reversine. The levels of apoptosis
(both early and late apoptosis) in ARO, WRO and SW579 cells
with reversine (10 uM) treatment were SW579 > ARO>
WRO, and were SW579 0 ARO>WRO with 1 or 5 uM
reversine treatment.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:02:34 GMT 2025
by
admin
on
Mon Mar 31 19:02:34 GMT 2025
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| Record UNII |
Z499CLJ023
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| Record Status |
Validated (UNII)
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| Record Version |
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REVERSINE
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TARGET -> INHIBITOR |
ANTAGONIST
IC50
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ACTIVE MOIETY |
